I know the bigger companies may charge a little extra but i know they will be reliable and licensed.

Agreed, the more parties involved usually the more difficult.

Also, if you setup a servicing company to manage the payments (usually like $25-35 a month), they can setup an escrow account for taxes and insurance as well and cut a check to her Trust bank account each month.

Usually 80% LTV is the max for investment.

I just want the extra monthly income and in 20 years be able to see how much equity I acquired and continue to invest as time goes.

I had some extra cash from painting houses in the summer and didn’t have to use that cash for college tuition since I was approved for a a student loan as well.

We help our clients with these strategies on a daily basis and they usually wipe out significant w2 tax liability. 

The reality is that the residents are usually there and willing to share all kinds of things. 

See my comments above to give them extra cashflow. 

That box usually has a different meaning as you suspect.I'd call the city and get a Permit History...see what was done during the remodel.